Sulfurized olefin compounds are widely produced and are known to be effective extreme pressure agents or load carrying additives for lubricating oils. (See U.S. Pat. Nos. 3,703,504; 3,697,499 and 3,471,404.) These sulfurized olefins may be obtained by sulfohalogenating a hydrocarbon olefin with a sulfur halide such as a sulfur chloride to form an alkylene sulfohalogenated complex. This complex can be further sulfurized such as by treating with an aqueous alkali metal monosulfide solution (see U.S. Pat. No. 3,703,504) and dehalogenating.
U.S. Pat. No. 4,200,546 discloses a process wherein sulfurized olefins are obtained via a process which comprises sulfohalogenating an olefin with a sulfur halide in the presence of a catalytic quantity (i.e., 0.2-10 wt.% based on the halide) of the lower aliphatic alcohol having up to above 10 carbon atoms (e.g., methanol, ethanol, propanol, i-propanol, butanol, i-butanol, etc.) to form a sulfohalogenated organic intermediate, and thereafter sulfurizing and dehalogenating said intermediate in the presence of a substantial quantity of lower aliphatic alcohol, e.g., from 10 to about 50% by weight of the adduct by treatment with an aqueous alkali metal sulfide solution, or an aqueous alkali metal monosulfide solution (which can be derived, for example, from a spent aqueous alkali metal hydroxide effluent from hydrocarbon purification) having a substantial combined sulfur content, thus producing an organic sulfide of high combined sulfur content.
U.S. Pat. No. 3,703,504, like the above referred to patent, discloses a process which comprises sulfohalogenating an olefin. The process is carried out with a sulfur halide in the presence of a catalytic quantity of a lower aliphatic alcohol to form a sulfohalogenated organic intermediate, and thereafter sulfurizing and dehalogenating said intermediate in the presence of a substantial quantity of a lower aliphatic alcohol by treatment with an aqueous alkali metal monosulfide solution derived from a spent aqueous alkali metal hydroxide effluent from hydrocarbon purification and having a substantial combined sulfur content in producing an organic sulfide of high combined sulfur content.
U.S. Pat. No. 3,706,724 discloses a process comprising (1) preparing a catalyzed chlorinated polyolefin by substantially uniformly admixing from about 0.25 to 0.5 part by weight of a Lewis acid per 100 parts of a comminuted chlorinated polyolefin (phr.), (2) maintaining the catalyzed chlorinated polyolefin in the form of the fluidized bed in the presence of a substantially inert gas and further in the presence of from about 2 to 5 phr. of an inert filler which has an affinity for adsorption onto the surfaces of the chlorinated polyolefin, (3) heating the fluidized bed to a temperature sufficient to produce the dehydrochlorination reaction without burning or charring the chlorinate polyethylene being dehydrochlorinated, then (4) cooling the fluidized bed and recovering the dehydrochlorinated product.
U.S. Pat. No. 3,862,991 discloses a bis(beta-chlorobeta-arylalkyl)disulfide, which is made by reacting sulfur monochloride with a beta-arylolefin selected from the group consisting of styrene, alpha-methyl styrene, p-tert-butyl styrene, o-chlorostyrene, p-chlorostyrene, vinyltoluene, anethole, 1,2-dihydroanaphthalene, acenaphthalene, 1-phenylcyclohexane and indene.
U.S. Pat. No. 2,322,258 discloses heating an olefin with a solution of potassium hydroxide in a monohydric alcohol such as ethanol. Polyhydric alcohols and hydroxy ethers are used for splitting a hydrogen halide from the molecule of a halogenated organic compound with an alkali. By carrying such reaction out in the presence of a polyhydric alcohol or a hydroxy ether, either sodium hydroxide or potassium hydroxide may be used as the alkaline reactant and the latter may be employed in solid form or dissolved in an alcohol or water, as desired.